Studies on Spiroheterocycles, Part II: Heterocyclization of the Spiro Compounds Containing Cyclohexanone and Thiobarbituric Acid with Different Bidentate Nucleophilic Reagents

Behera, Ratikanta; Behera, Ajay Kumar; Pradhan, Rosy; Pati, Anita

doi:10.1080/00397910600946231

Cited by 36 publications

(10 citation statements)

References 8 publications

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“…We noted that, the Cl2 and Cl4 atoms are in close contact to O8-atom where the Cl-O intramolecular distance is predicted around 3.3 Å. This could explain the different natural charges at [11][12] 1.394 1.381 A(10-48-50) 109.7 109.5 R (11)(12)(13)(14)(15)(16)(17)(18)(19) 1.404 1.399 A(10-48-51) 109.7 109.5 R 12-141.387 1.364 A (12-11-19) 122.2 121.8 R 14-151.390 1.369 A (11-12-14) 119.2 119.4 R 15-171.389 1.386 A (11-19-17) 116.3 116.1 R(17- 19) 1.404 1.392 A (11-19-20) 122 . [11][12] 116.1 116.9 A (26-29-35) 111.1 110.9 A(1- [11][12][13][14][15][16][17][18][19] 121.7 121.3 A (31-29-35) 114.3 115.6 A(2- 119.3 119.5 A (29-31-32) 111.0 114.5 A (2-14-15) 119.9 118.9 A (29-31-34) 105.9 107.8 A(3- 121.7 120.7 A (29-35-36) 122.7 120.7 A(3- [36][37] 116.1 116.3 A (29-35-42) 121.0 124.0 A (4-39-37) 119.3 118.8 A (32-31-34) 115.1 114.0 A (4-39-40) 119.9 120.3 A (36-35-42) 116.3 115.3 A (5-25-22) 122.2 121.4 A (35-36-37) 122.2 123.0 A (5-25-26) 122.2 120.8 A (35-42-40)...…”

Section: Natural Atomic Chargementioning

confidence: 98%

“…[4][5][6][7][8][9][10] However, current literature reveals that some diazaspiro [5.5]undecane-1,3,5,9tetraones motif possess a variety of therapeutic and biological properties such as anticonvulsant, 11 antifungicidal, 12 potent sedative-hypnotic, 13 antibacterial 14 and CNS depressant properties. 15 Moreover, this type of compounds can also be used as a yellow organic pigment and as a disperse dye with strong fluorescence property as it contains barbituric acid moiety. 16 Michael addition reaction is one of the remarkable 2040 Mohammad Shahidul Islam et al tool for C-C bond constructing process 17 especially, intermolecular double-Michael reaction which is the most powerful tool for the synthesis of spirocyclic product from the non-cyclic starting materials.…”

Section: Introductionmentioning

confidence: 99%

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Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4- diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies

et al. 2015

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Crystals of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4-diazaspiro[5.5]undecane-1,3,5,9tetraone were grown in polar solvents and subjected to single crystal X-ray diffraction. The molecular crystal is Triclinic, P-1, a = 8.3734 (19) Å, b = 12.382 (3) Å, c = 12.871 (3) Å, α = 66.639 (7) • , β = 85.148 (7) • , γ = 70.690 (6) • , V = 1154.5 (5)Å 3 , Z = 2, D calc = 1.519 g cm −3. The optimized molecular structure of the studied compound using B3LYP/6-311G(d,p) method showed good agreement with the X-ray structure. The electronic and spectroscopic properties of the title compound were predicted. The NBO calculations were used to calculate the natural atomic charges at the different atomic sites as well as the intramolecular charge transfer (ICT) interactions among the most significant natural orbitals. The high LP(N)→ BD*(2)C-O ICT interaction energies indicate strong electron delocalization from the lone pair of the N-atoms of the pyrimidinetrione ring to the adjacent carbonyl groups. In contrast, the small LP(O)→BD*(1)C-H stabilization energies (E (2)) indicated weak C-H-O interactions. Experimentally, the studied compound showed the most intense electronic transition band at 232 nm which is calculated using TD-DFT method as a shoulder at 231.3 nm (f=0.0832) and it belongs to H-3/H-1→L+1 and H-2→L+2 excitations. The GIAO calculated 1 H and 13 C NMR chemical shifts showed good correlations with the experimental data.

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Section: Natural Atomic Chargementioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4- diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies

et al. 2015

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“…As an example, we can highlight the fact that some diazaspiro[5.5]-undecane-1,3,5,9-tetraone motifs have a large range of therapeutic and biological properties such as anticonvulsant [10], potent sedative-hypnotic [11], CNS depressant properties [12], anti-fungicidal [13], and antibacterial activity [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Structure and Spectroscopic Investigations of Novel Fluorinated Spiro Heterocycles

et al. 2015

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This paper describes an efficient and regioselective method for the synthesis of novel fluorinated spiro-heterocycles in excellent yield by cascade [5+1] double Michael addition reactions. The compounds 7,11-bis(4-fluorophenyl)-2,4-dimethyl-2,4-diazaspiro[5.5] undecane-1,3,5,9-tetraone (3a) and 2,4-dimethyl-7,11-bis (4-(trifluoromethyl)phenyl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone (3b) were characterized by single-crystal X-ray diffraction, FT-IR and NMR techniques. The optimized geometrical parameters, infrared vibrational frequencies and NMR chemical shifts of the studied compounds have also been calculated using the density functional theory (DFT) method, using Becke-3-Lee-Yang-Parr functional and the 6-311G(d,p) basis set. There is good agreement between the experimentally OPEN ACCESSMolecules 2015, 20 8224 determined structural parameters, vibrational frequencies and NMR chemical shifts of the studied compounds and those predicted theoretically. The calculated natural atomic charges using NBO method showed higher polarity of 3a compared to 3b.The calculated electronic spectra are also discussed based on the TD-DFT calculations.

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“…Удобными многоцентровыми субстратами для синтеза разнообразных гетероциклических систем являются легкодоступные сопряженные диарилметилиденалканоны [1]. Наличие диенонового фрагмента предполагает возможность протекания реакций диполярного циклоприсоединения [2,3], конденсации [3][4][5][6], карбо-и гетероциклизации [7][8][9]. Ранее были изучены превращения бисарилметилиденалканонов с одинаковыми периферическими заместителями [4,6].…”

unclassified

“…Наличие диенонового фрагмента предполагает возможность протекания реакций диполярного циклоприсоединения [2,3], конденсации [3][4][5][6], карбо-и гетероциклизации [7][8][9]. Ранее были изучены превращения бисарилметилиденалканонов с одинаковыми периферическими заместителями [4,6]. Сведения относительно использования диенонов несимметричного строения носят ограниченный характер [10,11].…”

unclassified

Synthesis of Spiro-fused Hydropyrimidinthiones with Use of Thiobarbituric Acid

Klochkova¹,

Anis’kov²,

Schekina³

et al. 2016

CBE

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Найдены условия препаративного синтеза спиросочлененных гидропиримидинтионов на основе карбонильных субстратов и тиобарбитуровой кислоты. Представлены схемы конденсации, карбо-и гетероциклизации. Установлена регио-и стереонаправленность процессов. Ключевые слова: тиобарбитуровая кислота, моноеноны, диеноны, спиропиримидины, карбоциклизация, мультикомпонентные реакции, тандемные, каскадные процессы, домино-реакции.

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Studies on Spiroheterocycles, Part II: Heterocyclization of the Spiro Compounds Containing Cyclohexanone and Thiobarbituric Acid with Different Bidentate Nucleophilic Reagents

Cited by 36 publications

References 8 publications

Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4- diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies

Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4- diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies

Synthesis, Molecular Structure and Spectroscopic Investigations of Novel Fluorinated Spiro Heterocycles

Synthesis of Spiro-fused Hydropyrimidinthiones with Use of Thiobarbituric Acid

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